How to avoid these 5 biggest career regrets

Career regrets, whether we admit it or not, are part of the American Dream and its star-spangled ethos–an inseparable entity from the careers we choose. After all, they are how we get those white picket fences encircling the beautiful, sprawling front yard lawns; the two children, and the money to sustain these boons.

But as we plot the paths of our careers, we are destined for inevitable missteps, no matter how carefully we plan our quest. Even the best of us make miscalculations, mistakes, and sometimes even go so far as choosing the wrong careers. Surprisingly, the biggest career regrets are not those formed in failing to climb the corporate ladder or make bigger paychecks, but rather the missed opportunities to take control of our destinies — both collective destinies and individual ones alike.

To ensure you don’t retire with feelings of rue, read the most common career regrets below and remember them during the daily grind — the gems of truth may pay off for you in the long run.

Not Continuing Your Education

Education is a very broad term, and it means many different things depending on with whom you discuss the topic. However, one thing is not debatable: Education is more accessible than it’s ever been, and there are more cost-effective resources available to learn today than ever before. For instance, taking technology courses that provide you with webinar-based continuing professional education (CPE) credit and teach you how to leverage document management technologies to grow your skill set, can serve you long- term.

This will become especially true as software vendors provide more user certifications for the tools they develop.

How to Avoid the Regret: Although technology is increasingly the lens through which we learn, it will soon become the medium by which we not only learn our skill set, but demonstrate our skill set to others. Take a coding class from Treehouse or learn to use marketing analytics tools to boost your web presence should you decide to go in to business for yourself (see the next entry).

Never Working for Yourself

The man is always going to take more of your paycheck than he or she deserves. Recent studies even suggest that if the per capita income of the average American 50 years ago was adjusted to today’s earnings, the median worker would be making over $90,000 annually. The median income rests at about $32,000 per year.

How to Avoid the Regret: Document management for home use makes this possible for client-oriented consultants, freelancers, and more. Working for yourself and earning your own paychecks become more feasible when you have the efficiency of two people, and with only one pair of hands. Combine that with avoiding skyrocketing commercial real estate costs, and you have an easier path to startup success, whatever industry you decide to begin a business in.

Working Too Hard

Your life’s work should never be fully encapsulated by work itself. A significant body of research suggests working too many hours releases dopamine triggers in the brain also associated with habitual drug use — signifying that the motives behind “workaholism” are not to be glorified, but instead treated as a psychological condition.

There is far too much that goes into life outside of work — love, relationships, family, crossing off items on the bucket list, etc. Although hard work is an enormous merit, at a certain point it will only
impede one’s happiness.

How to Avoid the Regret: The 4-hour workweek (link to this) requires using the tools we need to become more efficient—not for greater economic output, but so we can live a better work-life balance, like the Scandinavian countries, who reputedly take as many as 3 months of paid leave per year.

Letting Bad Processes Keep You from Your Passion

Everyone wants to be a doctor, lawyer, or movie star until they learn about the steps needed to embark on these career paths—all of which are extremely rigorous and demanding. Modern office environments conjure feelings of drear not because the workers aren’t fit for the positions they hold, but because the processes of the office reduce most office activity to boring, trivial minutiae. Have you ever heard someone say something like “I love my job, but the stuff that comes with it makes it hard to focus on the parts of it that I do enjoy”? Chances are you have, and you may have even chirped a similar expression yourself.

In most cases, these feelings of minutia can be traced to trying to run 21st-century businesses with 19th-century mediums—paper-based documentation, and filing cabinets, which were invented over a hundred years
ago by Edwin G. Seibels.

How to Avoid the Regret: If a thousand paper-based processes stand between you and helping a new client, your passion for customer service is going to dwindle.

If you fear a fax machine will leave blurred details on a document you send to an important vendor with whom you do business, the process itself will invoke fear, not excitement.

If you send un-encrypted email attachments without an encrypted web portal, you’ll run the risk of letting client data be intercepted, and the fear of this alone is enough to stave off the enjoyment you entered the profession to acquire.

Avoiding Failure

Failure itself is not a bad thing. Taking chances produces discomfort, but this discomfort is the only way we can ever grow. Most inventors and historically significant people understood this. These failures alone did not result in them having career regrets, but they did put their path to success in proper light.

Thomas Edison even said upon struggling to invent the light bulb that he had not failed, but rather found 10,000 ways that don’t work when it comes to, well, making a light bulb. And Einstein constantly challenged his contemporaries to think differently, accepting the onus of social disgrace that came with it.

That said, failure remains something we should prepare ourselves for. If we go skiing without a helmet and intend to perform a back-flip, we aren’t adequately preparing ourselves to tackle new challenges with poise and confidence, because we are exposing ourselves to too much risk. In the event of failure, permanent injury could be caused, or, even worse, death. Wearing a helmet cushions our falls and helps us feel safer in taking calculated risks. This is just part of career regrets when we apply the same concept to the office.

This precept applies to our careers. If we attempt to take big leaps of faith in career advancement without preparing ourselves for the event of failure, our growth will be stymied and we will end up worse than we were prior to taking the risk.

How to Avoid the Regret: Learning to use a document management system to cushion our risks in handling information can help us take greater risks as professionals. For instance, the mobile applications of these systems let us experiment with technology in client-facing contexts.

And the more we expose ourselves to this discomfort, the more rewarding it will be when clients get the service they need through that technology.

Jesse Wood
is the CEO of document management software vendor, eFileCabinet. Founded in 2001, eFileCabinet, Inc. began as a cutting-edge tool to digitally store records in accounting firms. As it grew in popularity, eFileCabinet developed into a full-fledged electronic document management solution designed to help organizations automate redundant processes, ensure security, and solve common office problems.